My friend Edgar is dating again. He’s 52, recently single after 20 years of marriage, and completely fucking terrified of women under 45.

He called me last week. “My sister says I need to stop spending $400 on first dates. That I’m trying too hard.”

Who the hell is Edgar taking to dinner? “Just regular women,” he says. “From the apps.”

Edgar. If a man spends $400 on a first date with me I assume one of three things:

I’m being compensated for sex and he’s too civilized to name it directly. Like he’s hoping I’ll intuit the terms somewhere between the Sauternes and the check. One.

He’s planning to skin me. The expensive dinner is his apologetic overture to the universe before he commits something irreversible. Two.

He inherited his money and fundamentally misunderstands what currency represents. Tips poorly and assumes generosity scales with zeroes. Three.

None of these scenarios end with us, together, in bed.

Men complain that women are gold diggers. Women complain that men think money replaces personality. We’re both right and both wrong. Here’s what’s missing: the question isn’t how much money you spend. The question is what it’s telling her about you. So, let me lay out a little roadmap for you, an inside look at what women really want when it comes to money and dating. Consider this your Pleasure Protocol.

First Dates: Don’t Be Terrified

The best first date I ever had cost $12. A man took me to a used bookstore and bought me three paperbacks based on a 10-minute conversation. I fucked him that night because he’d been paying attention instead of performing.

The $400 dinner tells her you’re panicking, that you think money replaces having something to say. Instead of forgoing personality for cash, show her what you actually like. Take her somewhere you’d go anyway. The bookstore reading you were planning to attend. The bar with the jazz trio. The taco place you’ve been going to for 10 years. The museum exhibit you actually want to see.

If she wants Michelin stars and champagne on date one, she can find that elsewhere. You’re showing her who you are, not auditioning for the role of ATM.

Cost: $40. Maybe $60 if you’re feeling generous.

When It’s Casual: The Hygiene Overlap

Bad at reading subtext? Terrible with cues? Don’t want to send flowers she might hate? Start with hygiene.

She wants her skin clear. You want her skin clear. She wants her hair to move like it costs money. You want that too. She wants to inhabit her body instead of apologize for it. So do you.

The $400 dinner evaporates by Wednesday. You both performed. She wore architectural clothing that restricts breathing. You pretended to distinguish Burgundy from Bordeaux. The food was fine. The lighting was flattering. Then it’s memory.

The facialist who lasers her face? Months. The $400 hair appointment instead of dinner? Four months minimum. Daily she feels like herself. Daily you benefit. A manicure costs half of dinner. She examines her hands for two weeks thinking about you. The colorist appointment she’s deferred for half a year? You just bought four months of her feeling capable. The massage she needs but won’t book? The oxygen facial? That absurdly expensive Korean serum she researches at 2am but refuses to justify?

Not profound. But devastatingly thoughtful.

If you’re running identical plays with different women—same restaurant, same weekend escape, same bedding you ordered once in 2019—they notice. You’re indifferent to particulars. You just want access. Crawl her Instagram for clues. Ask her directly who she sees for what. Then book it. That’s the difference.

Cost: you decide.

For Relationships: You Have Data Now

Now you’ve been observing. The headphones she won’t replace. The book she references cyclically. The shoulder pain she mentions every Sunday night. The housekeeper she won’t hire because “that’s for people with real money.”

She’s not asking you to provide these things. She’s just living her life out loud, so pay attention.

Early in our relationship, one of my boyfriends left for work for three weeks. I knew his habits. After dinner he used toothpicks. Not drugstore ones. The good ones. When he returned I placed cinnamon tea tree toothpicks in his hand after our first meal back.

Eight dollars. Two minutes on Amazon. That night he fucked me like I’d discovered penicillin. Not because toothpicks are costly, but because I’d been attending to something so minor he assumed invisibility.

Women start feeling invisible in relationships. Not because you’re neglecting us. Because we stop mentioning things. We mention the shoulder pain once, maybe twice. Then we stop. We’ve learned not to ask.

Construct an evening. Her preferred thing. Your preferred thing. Concert. Reading. Rave. Escape room. Ghost tour. You manage logistics. She arrives.

Cost: $150. She remembers it indefinitely.

The question isn’t whether you’ll spend money on your date. You will. The question is whether you’re oxidizing it or compounding it.

Open your ears. Or at minimum, understand the hygiene overlap.

Women ration. We prioritize everyone else. When someone tends to us without prompting, without requiring justification, without converting it to transaction—we remember permanently. We reciprocate differently. Better. More.

You’re spending the money regardless. Might as well understand what actually works.

She’ll come find you.